Compound for organic electronic element, organic electronic device using same, and electronic device thereof

ABSTRACT

Provided are an organic electronic element and an electronic device thereof, the organic electronic element being capable of achieving high light-emitting efficiency and a low driving voltage, and can also greatly improve the lifespan of the element by using a compound of the present invention as a phosphorescent host material.

BACKGROUND Technical Field

The present invention relates to compound for organic electronicelement, organic electronic element using the same, and an electronicdevice thereof.

Background Art

In general, organic light emitting phenomenon refers to a phenomenonthat converts electronic energy into light energy by using an organicmaterial.

An organic electronic element using an organic light emitting phenomenonusually has a structure including an anode, a cathode, and an organicmaterial layer interposed therebetween. Here, in order to increase theefficiency and stability of the organic electronic element, the organicmaterial layer is often composed of a multi-layered structure composedof different materials, and for example, may include a hole injectionlayer, a hole transport layer, an emitting layer, an electron transportlayer, an electron injection layer and the like.

A material used as an organic material layer in an organic electronicelement may be classified into a light emitting material and a chargetransport material, such as a hole injection material, a hole transportmaterial, an electron transport material, an electron injection materialand the like depending on its function.

In the case of a polycyclic compound containing a heteroatom, thedifference in properties according to the material structure is so largethat it is applied to various layers as a material of an organicelectronic element. In particular, it has characteristics of differentband gaps (HOMO, LUMO), electronical characteristics, chemicalproperties, and physical properties depending on the number of rings,fused positions and the type and arrangement of heteroatoms, thereforeapplication development for layers of various organic electronicelements using the same has been progressed.

As a representative example thereof, in the following Patent Documents 1to 4, the performance of the 5-membered cyclic compound in thepolycyclic compound has been reported depending on the hetero type,arrangement, substituent type, fused position, and the like.

[Patent Document 1]: U.S. Pat. No. 5,843,607

[Patent Document 2]: Japanese Laid-Open Patent Publication No.1999-162650

[Patent Document 3]: Korean Published Patent Application No.2008-0085000

[Patent Document 4]: US Patent Publication No. 2010-0187977

[Patent Document 5]: Korean Published Patent Application No.2011-0018340

[Patent Document 6]: Korean Published Patent Application No.2009-0057711

Patent Documents 1 and 2 disclose an embodiment in which theindolecarbazole core in which the hetero atom in the 5-membered cycliccompound is composed only of nitrogen (N) is used, and an aryl groupsubstituted or unsubstituted in N of indolocarbazole is used. However,in the prior invention 1, there exists only a simple aryl groupsubstituted or unsubstituted with an alkyl group, an amino group, analkoxy group, or the like as a substituent, so that the effect of thesubstituents of the polycyclic compounds was very poor to prove, andonly the use as a hole transport material is described, and the usethereof as a phosphorescent host material is not described.

Patent Documents 3 and 4 disclose a compound in which pyridine,pyrimidine, triazine or the like containing an aryl group and N,respectively, were substituted for an indolecarbazole core having ahetero atom N in the same 5-membered cyclic compound as in the abovePatent Documents 1 and 2, however only the use examples forphosphorescent green host materials are described, and the performancefor other heterocyclic compounds substituted for indolecarbazole core isnot described.

In Patent Documents 5, Nitrogen (N), oxygen (O), sulfur (S), carbon andthe like are described as heteroatom in the 5-membered cyclic compound,however there are only examples using the same heteroatom in theperformance measurement data, the performance characteristics of a5-membered cyclic compound containing a different heteroatom could notbe confirmed.

Therefore, the patent document does not disclose solutions to low chargecarrier mobility and low oxidation stability of a 5-membered cycliccompound containing same heteroatom.

When the 5-membered cyclic compound molecules are generally laminated,as the adjacent π-electrons increase, they have a strong electronicalinteraction, and this is closely related to the charge carrier mobility,particularly, the same 5-membered cyclic compound of N—N type has anedge-to-face morphology as an order of arrangement of molecules whenmolecules are laminated, otherwise a different 5-membered cycliccompound with different heteroatoms has an antiparallel cofacialπ-stacking structure in which the packing structure of the molecules isopposite to each other, so that the arrangement order of the moleculesbecomes face-to-face morphology. It is reported that the steric effectof the substituent substituted on the asymmetrically arranged heteroatom N as the cause of this laminated structure causes relatively highcarrier mobility and high oxidation stability (Org. Lett. 2008, 10,1199).

In Patent Document 6, an example of using as a fluorescent host materialfor various polycyclic compounds having 7 or more membered cycliccompounds has been reported.

As described above, the fused positions, the number of rings, thearrangement of heteroatoms, and characteristic change by type of thepolycyclic compounds have not yet been sufficiently developed.

Particularly, in a phosphorescent organic electronic element using aphosphorescent dopant material, the LUMO and HOMO levels of the hostmaterial have a great influence on the efficiency and life span of theorganic electronic element, this is because the charge balance controlin the emitting layer, the quenching of the dopant, and the reduction inefficiency and life span due to light emission at the interface of thehole transport layer can be prevented, depending on whether electron andhole injection in the emitting layer can be efficiently controlled.

For fluorescent and phosphorescent host materials, recently we have beenstudying the increase of efficiency and life span of organic electronicelements using TADF (thermal activated delayed fluorescent), exciplex,etc., particularly, and many studies have been carried out to identifythe energy transfer method from the host material to the dopantmaterial.

Although there are various methods for identifying the energy transferin the emitting layer for TADF (thermally activated delayed fluorescent)and exciplex, it can be easily confirmed by the PL lifetime (TRIP)measurement method.

The TRIP (Time Resolved Transient PL) measurement method is a method ofobserving a decay time over time after irradiating the host thin filmwith a pulsed light source, and therefore it is possible to identify theenergy transfer method by observing the energy transfer and the lagtime. The TRTP measurement can distinguish between fluorescence andphosphorescence, an energy transfer method in a mixed host material, anexciplex energy transfer method, and a TADF energy transfer method.

There are various factors affecting the efficiency and life spandepending on the manner in which the energy is transferred from the hostmaterial to the dopant material, and the energy transfer method differsdepending on the material, so that the development of stable andefficient host material for organic electronic element has not yet beensufficiently developed. Therefore, development of new materials iscontinuously required, and especially development of a host material foran emitting layer is urgently required.

DETAILED DESCRIPTION OF THE INVENTION Summary

The present invention relates to a compound capable of improving chargebalance adjustment, efficiency and lifetime in an emitting layer bycontrolling the energy level of a host material of a phosphorescentemitting organic electric element including a phosphorescent dopant, andan organic electric element using the same and an electronic devicethereof.

Technical Solution

By containing a specific host as a main component for controlling theefficient hole injection in the emitting layer of the phosphorescenceemitting organic electronic element, the present invention provides acompound capable of improving charge balance adjustment, efficiency andlifetime in the emitting layer, and an organic electric elementincluding the same.

In another aspect, the present invention also provides an organicelectronic element using the compound represented by the above Formulasand an electronic device thereof.

Effects of the Invention

By using the mixture according to the present invention as aphosphorescent host material, it is possible to achieve a high luminousefficiency and a low driving voltage of an organic electric element, andthe life span of the device can be greatly improved.

BRIEF DESCRIPTION OF THE DRAWINGS

The FIGURE is an illustration of an organic electroluminescent deviceaccording to the present invention.

100: organic electric element, 110: substrate 120: the firstelectrode(anode), 130: the hole injection layer 140: the hole transportlayer, 141: a buffer layer 150: the emitting layer, 151: the emittingauxiliary layer 160: the electron transport layer, 170: the electroninjection layer 180: the second electrode(cathode)

DETAILED DESCRIPTION

Hereinafter, some embodiments of the present invention will be describedin detail. Further, in the following description of the presentinvention, a detailed description of known functions and configurationsincorporated herein will be omitted when it may make the subject matterof the present invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used to define an essence, order orsequence of a corresponding component but used merely to distinguish thecorresponding component from other component(s). It should be noted thatif a component is described as being “connected”, “coupled”, or “linked”to another component, the component may be directly connected orconnected to the other component, but another component may be“connected”, “coupled” or “linked” between each component.

As used in the specification and the accompanying claims, unlessotherwise stated, the following is the meaning of the term as follows.

Unless otherwise stated, the term “halo” or “halogen”, as used herein,includes fluorine, bromine, chlorine, or iodine.

Unless otherwise stated, the term “alkyl” or “alkyl group”, as usedherein, has a single bond of 1 to 60 carbon atoms, and means saturatedaliphatic functional radicals including a linear alkyl group, a branchedchain alkyl group, a cycloalkyl group (alicyclic), an cycloalkyl groupsubstituted with a alkyl or an alkyl group substituted with acycloalkyl.

Unless otherwise stated, the term “haloalkyl” or “halogen alkyl”, asused herein, includes an alkyl group substituted with a halogen.

Unless otherwise stated, the term “heteroalkyl”, as used herein, meansalkyl substituted one or more of carbon atoms consisting of an alkylwith hetero atom.

Unless otherwise stated, the term “alkenyl” or “alkynyl”, as usedherein, has double or triple bonds of 2 to 60 carbon atoms, but is notlimited thereto, and includes a linear or a branched chain group.

Unless otherwise stated, the term “cycloalkyl”, as used herein, meansalkyl forming a ring having 3 to 60 carbon atoms, but is not limitedthereto.

Unless otherwise stated, the term “alkoxyl group”, “alkoxy group” or“alkyloxy group”, as used herein, means an oxygen radical attached to analkyl group, but is not limited thereto, and has 1 to 60 carbon atoms.

Unless otherwise stated, the term “alkenoxyl group”, “alkenoxy group”,“alkenyloxyl group” or “alkenyloxy group”, as used herein, means anoxygen radical attached to an alkenyl group, but is not limited thereto,and has 2 to 60 carbon atoms.

Unless otherwise stated, the term “aryloxyl group” or “aryloxy group”,as used herein, means an oxygen radical attached to an aryl group, butis not limited thereto, and has 6 to 60 carbon atoms.

Unless otherwise stated, the term “aryl group” or “arylene group”, asused herein, has 6 to 60 carbon atoms, but is not limited thereto.Herein, the aryl group or arylene group means a monocyclic andpolycyclic aromatic group, and may also be formed in conjunction with anadjacent group. Examples of “aryl group” may include a phenyl group, abiphenyl group, a fluorene group, or a spirofluorene group.

The prefix “aryl” or “ar” means a radical substituted with an arylgroup. For example, an arylalkyl may be an alkyl substituted with anaryl, and an arylalkenyl may be an alkenyl substituted with aryl, and aradical substituted with an aryl has a number of carbon atoms as definedherein.

Also, when prefixes are named subsequently, it means that substituentsare listed in the order described first. For example, an arylalkoxymeans an alkoxy substituted with an aryl, an alkoxylcarbonyl means acarbonyl substituted with an alkoxyl, and an arylcarbonylalkenyl alsomeans an alkenyl substituted with an arylcarbonyl, wherein thearylcarbonyl may be a carbonyl substituted with an aryl.

Unless otherwise stated, the term “heteroalkyl”, as used herein, meansalkyl containing one or more of hetero atoms. Unless otherwise stated,the term “heteroaryl group” or “heteroarylene group”, as used herein,means a C2 to C60 aryl containing one or more of hetero atoms or arylenegroup, but is not limited thereto, and includes at least one ofmonocyclic and polycyclic rings, and may also be formed in conjunctionwith an adjacent group.

Unless otherwise stated, the term “heterocyclic group”, as used herein,contains one or more heteroatoms, but is not limited thereto, has 2 to60 carbon atoms, includes any one of monocyclic and polycyclic rings,and may include heteroaliphatic ring and/or heteroaromatic ring. Also,the heterocyclic group may also be formed in conjunction with anadjacent group.

Unless otherwise stated, the term “heteroatom”, as used herein,represents at least one of N, O, S, P, or Si.

Also, the term “heterocyclic group” may include a ring containing SO₂instead of carbon consisting of cycle. For example, “heterocyclic group”includes compound below.

Unless otherwise stated, the term “aliphatic”, as used herein, means analiphatic hydrocarbon having 1 to 60 carbon atoms, and the term“aliphatic ring”, as used herein, means an aliphatic hydrocarbon ringhaving 3 to 60 carbon atoms.

Unless otherwise stated, the term “ring”, as used herein, means analiphatic ring having 3 to 60 carbon atoms, or an aromatic ring having 6to 60 carbon atoms, or a hetero ring having 2 to 60 carbon atoms, or afused ring formed by the combination of them, and includes a saturatedor unsaturated ring.

Other hetero compounds or hetero radicals other than the above-mentionedhetero compounds include, but are not limited thereto, one or moreheteroatoms.

Unless otherwise stated, the term “carbonyl”, as used herein, isrepresented by —COR′, wherein R′ may be hydrogen, an alkyl having 1 to20 carbon atoms, an aryl having 6 to 30 carbon atoms, a cycloalkylhaving 3 to 30 carbon atoms, an alkenyl having 2 to 20 carbon atoms, analkynyl having 2 to 20 carbon atoms, or the combination of these. Unlessotherwise stated, the term “ether”, as used herein, is represented by—R—O—R′, wherein R or R′ may be independently hydrogen, an alkyl having1 to 20 carbon atoms, an aryl having 6 to 30 carbon atoms, a cycloalkylhaving 3 to 30 carbon atoms, an alkenyl having 2 to 20 carbon atoms, analkynyl having 2 to 20 carbon atoms, or the combination of these.

Unless otherwise stated, the term “substituted or unsubstituted”, asused herein, means that substitution is substituted by at least onesubstituent selected from the group consisting of, but is not limitedthereto, deuterium, halogen, an amino group, a nitrile group, a nitrogroup, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxyl group, a C₁-C₂₀ alkylaminegroup, a C₁-C₂₀ alkylthiopen group, a C₆-C₂₀ arylthiopen group, a C₂-C₂₀alkenyl group, a C₂-C₂₀ alkynyl group, a C₃-C₂₀ cycloalkyl group, aC₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted by deuterium, aC₈-C₂₀ arylalkenyl group, a silane group, a boron group, a germaniumgroup, and a C₂-C₂₀ heterocyclic group.

Unless otherwise expressly stated, the Formula used in the presentinvention, as used herein, is applied in the same manner as thesubstituent definition according to the definition of the exponent ofthe following Formula.

Wherein, when a is an integer of zero, the substituent R¹ is absent, andwhen a is an integer of 1, the sole substituent R¹ is linked to any oneof the carbon constituting the benzene ring, and when a is an integer of2 or 3, they are respectively combined as follows, wherein R¹ may be thesame or different from each other. When a is an integer from 4 to 6, itis bonded to the carbon of the benzene ring in a similar manner, whilethe labeling of the hydrogen bonded to the carbon forming the benzenering is omitted.

Unless otherwise expressly stated, the terms “ortho”, “meta”, and “para”used in the present invention refer to the substitution positions of allsubstituents, and the ortho position indicates the position of thesubstituent immediately adjacent to the compound, for example, whenbenzene is used, it means 1 or 2 position, and the meta position is thenext substitution position of the neighbor substitution position, whenbenzene as an example stands for 1 or 3 position, and the para positionis the next substitution position of the meta position, which means 1and 4 position when benzene is taken as an example. A more detailedexample of the substitution position is as follows, and it can beconfirmed that the ortho-, and meta-position are substituted bynon-linear type and para-positions are substituted by linear type.

[Example of Ortho-Position]

[Example of Meta-Position]

[Example of Para-Position]

Hereinafter, a compound according to an aspect of the present inventionand an organic electric element comprising the same will be described.

The present invention provides a compound represented by Formula 1.

{in Formula 1,1) X is N-L²-Ar², O or S,2) Ar¹ and Ar² are each independently selected from the group consistingof hydrogen; deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group;a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N,S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and-L′-N(R^(a))(R^(b));3) a and b are an integer of 0 to 4, and c is an integer of 0 to 6,4) R¹, R² and R³ are the same or different from each other, and are eachindependently selected from the group consisting of hydrogen; deuterium;halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclicgroup including at least one heteroatom of O, N, S, Si or P; a fusedring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; aC₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; aC₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R^(a))(R^(b));or in case a, b and c are 2 or more, and R¹, R² and R³ are each inplural being the same or different, and a plurality of R¹ or a pluralityof R² or a plurality of R³ may be bonded to each other to form a ring.5) L¹ and L² are each independently selected from the group consistingof a single bond; a C₆-C₆₀ arylene group; and a fluorenylene group; afused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring;and a C₂-C₆₀ heterocyclic group;6) L′ is selected from the group consisting of a single bond; a C₆-C₆₀arylene group; and a fluorenylene group; a fused ring group of a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclicgroup; and R^(a) and R^(b) are each independently selected from thegroup consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a fused ringgroup of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and aC₂-C₆₀ heterocyclic group containing at least one hetero atom of O, N,S, Si, or P,wherein, the aryl group, fluorenyl group, arylene group, heterocyclicgroup, fluorenylene group, fused ring group, alkyl group, alkenyl group,alkoxy group and aryloxy group may be substituted with one or moresubstituents selected from the group consisting of deuterium; halogen; asilane group substituted or unsubstituted with C₁-C₂₀ alkyl group orC₆-C₂₀ aryl group; siloxane group; boron group; germanium group; cyanogroup; nitro group; -L-N(R^(a))(R^(b)); a C₁-C₂₀ alkylthio group; C₁-C₂₀alkoxyl group; C₁-C₂₀ alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynylgroup; C₆-C₂₀ aryl group; C₆-C₂₀ aryl group substituted with deuterium;a fluorenyl group; C₂-C₂₀ heterocyclic group; C₃-C₂₀ cycloalkyl group;C₇-C₂₀ arylalkyl group; and C₈-C₂₀ arylalkenyl group; wherein thesubstituents may combine each other and form a saturated or unsaturatedring, wherein the term ‘ring’ means a C₃-C₆₀ aliphatic ring or a C₆-C₆₀aromatic ring or a C₂-C₆₀ heterocyclic group or a fused ring formed bythe combination of thereof.}

The compound represented by Formula 1 is represented by any one of thefollowing Formulas 2 to 4.

{in Formulas 2 to 4,R¹, R², R³, L¹, L², Ar¹, Ar², a, b and c are the same as defined above}

Ar¹ and Ar² in Formula 1 are represented by Formula A-1 or A-2.

{in Formulas A-1 or A-2,1) Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, Q⁷, Q⁸ and Q⁹ are each independently N orCR^(e),2) R^(e) is selected from the group consisting of hydrogen; deuterium;halogen; a silane group substituted or unsubstituted with C₁-C₂₀ alkylgroup or C₆-C₂₀ aryl group; siloxane group; boron group; germaniumgroup; cyano group; nitro group; a C₁-C₂₀ alkylthio group; C₁-C₂₀alkoxyl group; C₁-C₂₀ alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynylgroup; C₆-C₂₀ aryl group; C₆-C₂₀ aryl group substituted with deuterium;a fluorenyl group; C₂-C₂₀ heterocyclic group; containing at least onehetero atom of O, N, S, Si, or P, C₃-C₂₀cycloalkyl group; C₇-C₂₀arylalkyl group; and C₈-C₂₀ arylalkenyl group;3) Z is any one of Formulas C-1 to C-15,

wherein the mark * represents a bonding moiety which combines with thering including Q1 to Q4 to form a fused ring,4) in Formulas C-1 to C-15,W¹ and W² are single bond, N-L³-Ar³, S, O or C(R^(f))(R^(g)),5) V is each independently N or CR^(h),6) L³ is selected from a single bond; a C₆-C₆₀ arylene group; and afluorenylene group; C₂-C₆₀ divalent heterocyclic group containing atleast one hetero atom of O, N, S, Si, or P; a divalent fused ring groupof a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a divalentaliphatic hydrocarbon group;7) Ara, R^(f), R^(g) and R^(h) are each independently selected from thearyl group, fluorenyl group, a C₂-C₆₀ heterocyclic group including atleast one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; aC₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; aC₆-C₃₀ aryloxy group; R^(f) and R^(g) may be bonded to each other toform a spiro together with the carbon (C) to which they are bonded.}

The present invention also provides the following compounds 1-1 to 1-101comprised in Formula 1.

In the above Formulas of the present invention, when Ar¹, Ar², Ar³ andR¹, R², R³ are aryl groups, it is preferably C₆-C₃₀ aryl group, morepreferably C₆-C₂₄ aryl group, and when Ar¹, Ar², Ar³ and R¹, R², R³ areheterocyclic groups, it is preferably a C₂-C₄₀ heterocyclic group, morepreferably a C₂-C₃₀ heterocyclic group, still more preferably a C₂-C₂₄heterocyclic group.

when Ar¹, Ar², Ar³ and R¹, R², R³ are aryl groups, specific examplesthereof include phenyl, biphenyl, terphenyl, quaterphenyl, stylbenyl,naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klycenyl group,and the like. When Ar¹, Ar², Ar³ and R¹, R², R³ are heterocyclic groups,specific examples thereof include a thiophene group, a furan group, apyrrole group, an imidazole group, a thiazole group, an oxazole group,an oxadiazole group, a triazole group, a pyridyl group, a bipyridylgroup, a pyrimidyl group, a triazine group, a pyrazine group, a triazolegroup, an acridyl group, a pyridazine group, a pyrazinyl group, aquinolinyl group, a quinazolinyl group, a quinoxalinyl group, abenzoquinoxaline, a dibenzoquinoxaline, a phthalazinyl group, apyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinylgroup, an isoquinoline group, an indole group, a carbazole group,indolocarbazole, acridine, phenoxazine, benzopyridazine,benzopyrimidine, carboline, benzocarboline, benzoxazole group, abenzoimidazole group, a benzothiazole group, a benzocarbazole group, abenzothiophene group, dibenzothiophene group, a benzofuranyl group, aphenanthroline group, a thiazolyl group, an isoxazolyl group, anoxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, aphenothiazinyl group and dibenzofuranyl group, thienothiophene,benzothienopyridine, benzothienopyrimidine, benzofuropyrimidine,dimethylbenzoindenopyrimidine, phenanthrofuropyrimidine,naphthofuropyrimidine, naphthothienopyrimidine, dibenzothiophene group,thianthrene, dihydrobenzothiophenopyrazine, dihydrobenzofuropyrazine,and the like, but are not limited thereto.

Also, when L¹, L² and L³ in Formula of the present invention are anarylene group, it may preferably be an C₆-C₃₀ arylene group, morepreferably an C₆-C₁₈ arylene group, illustratively, it may be phenylene,biphenyl, terphenyl, naphthalene, anthracene, phenanthrene, and thelike. Preferably, L¹ is a heterocyclic group, it is preferably a C₂-C₃₀heterocyclic group, more preferably a C₂-C₁₈ heterocyclic group,illustratively, it can be dibenzofuran, dibenzothiophene, carbazole, andthe like, and when L¹ is a fluorenylene group, it can be exemplarily9,9-dimethyl-9H-fluorene.

Referring to the FIGURE, the organic electric element (100) according tothe present invention includes a first electrode (120) formed on asubstrate (110), a second electrode (180), and an organic material layerincluding the compound represented by Formula 1 between the firstelectrode (120) and the second electrode (180). Here, the firstelectrode (120) may be an anode (positive electrode), and the secondelectrode (180) may be a cathode (negative electrode). In the case of aninverted organic electric element, the first electrode may be a cathode,and the second electrode may be an anode.

The organic material layer may include a hole injection layer (130), ahole transport layer (140), an emitting layer (150), an electrontransport layer (160), and an electron injection layer (170) formed insequence on the first electrode (120). Here, the remaining layers exceptthe emitting layer (150) may not be formed. The organic material layermay further include a hole blocking layer, an electron blocking layer,an emitting-auxiliary layer (151), an electron transport auxiliarylayer, a buffer layer (141), etc., and the electron transport layer(160) and the like may serve as a hole blocking layer.

Although not shown, the organic electric element according to thepresent invention may further include a protective layer formed on atleast one side of the first and second electrodes, which is a sideopposite to the organic material layer.

Otherwise, even if the same core is used, the band gap, the electricalcharacteristics, the interface characteristics, and the like may varydepending on which substituent is bonded at which position, thereforethe choice of core and the combination of sub-substituents associatedtherewith is also very important, and in particular, when the optimalcombination of energy levels and T1 values and unique properties ofmaterials (mobility, interfacial characteristics, etc.) of each organicmaterial layer is achieved, a long life span and high efficiency can beachieved at the same time.

The organic electroluminescent device according to an embodiment of thepresent invention may be manufactured using a PVD (physical vapordeposition) method. For example, a metal or a metal oxide havingconductivity or an alloy thereof is deposited on a substrate to form acathode, and the organic material layer including the hole injectionlayer (130), the hole transport layer (140), the emitting layer (150),the electron transport layer (160), and the electron injection layer(170) is formed thereon, and then depositing a material usable as acathode thereon can manufacture an organic electroluminescent deviceaccording to an embodiment of the present invention.

In addition, an emission auxiliary layer (151) may be further formedbetween the hole transport layer (140) and the emitting layer (150), andan electron transport auxiliary layer may be further formed between theemitting layer (150) and the electron transport layer (160).

In addition, at least one hole transporting band layer is providedbetween the first electrode and the emitting layer, wherein the holetransporting band layer may include a hole transport layer, an emittingauxiliary layer or both, wherein the hole transporting band layerincludes an organic electronic element comprising the compoundrepresented by Formula 1.

The present invention may further include a light efficiency enhancinglayer formed on at least one of the opposite side to the organicmaterial layer among one side of the first electrode, or one of theopposite side to the organic material layer among one side of the secondelectrode.

Also, the present invention provides the organic electric elementwherein the organic material layer is formed by one of a spin coatingprocess, a nozzle printing process, an inkjet printing process, a slotcoating process, a dip coating process or a roll-to-roll process, andsince the organic material layer according to the present invention canbe formed by various methods, the scope of the present invention is notlimited by the method of forming the organic material layer.

As another specific example, the present invention provides an organicelectric element wherein the emitting layer in the organic materiallayer is a phosphorescent light emitting layer.

The organic electric element according to an embodiment of the presentinvention may be a front emission type, a back emission type, or aboth-sided emission type, depending on the material used.

WOLED (White Organic Light Emitting Device) has advantages of highresolution realization and excellent fairness, and can be manufacturedusing conventional LCD color filter technology. Various structures for awhite organic light emitting device mainly used as a backlight devicehave been proposed and patented. Representatively, there areside-by-side arrangement of the radiation part of the R (red), G (green)and B (blue), a stacking method in which R, G, and B emitting layers arelaminated on top and bottom, electroluminescence by the blue (B) organicemitting layer and, by using the light from this, a color conversionmaterial (CCM) method using a photo-luminescence of an inorganicphosphor, etc., and the present invention may be applied to such WOLED.

The present invention also provides an electronic device comprising adisplay device including the organic electric element; and a controlunit for driving the display device.

According to another aspect, the present invention provides an displaydevice wherein the organic electric element is at least one of an OLED,an organic solar cell, an organic photo conductor, an organictransistor(organic TFT) and an element for monochromic or whiteillumination. Here, the electronic device may be a wired/wirelesscommunication terminal which is currently used or will be used in thefuture, and covers all kinds of electronic devices including a mobilecommunication terminal such as a cellular phone, a personal digitalassistant (PDA), an electronic dictionary, a point-to-multipoint (PMP),a remote controller, a navigation unit, a game player, various kinds ofTVs, and various kinds of computers.

Hereinafter, Synthesis Examples of the compound represented by Formula 1of the present invention and preparation examples of the organicelectric element of the present invention will be described in detail byway of example, but are not limited to the following examples.

Synthesis Example 1

I. Synthesis of Formula 1

The final products 1 represented by Formula 1 of the present inventioncan be synthesized by reaction between Sub 1 and Sub 2 as illustrated inthe following Reaction Scheme 1.

1. Synthesis Example of Sub 1

Sub 1 of reaction scheme 1 can be synthesized by the reaction path ofthe following reaction scheme 2, but is not limited thereto.

Synthesis Example of Sub 1-1

(1) Synthesis of Sub 1-I-1

After 13-phenyl-13H-dibenzo[a,i]carbazole (60 g, 142.07 mmol),bis(pinacolato)diboron (39.68 g, 156.28 mmol), KOAc (41.83 g, 426.21mmol), PdCl₂(dppf) (3.48 g, 4.26 mmol) were dissolved in DMF (710 mL),and refluxed at 120° C. for 12 hours. When the reaction was completed,the temperature of the reaction was cooled to room temperature,extracted with CH₂Cl₂ and wiped with water. The organic layer was driedover MgSO₄ and concentrated. The resulting compound was recrystallizedby CH₂Cl₂ and methanol solvent to obtain the product. (58.02 g, 87%)

(2) Synthesis of Sub 1-II-1

Sub 1-I-1 (58.02 g, 132.05 mmol), 1-bromo-2-nitrobenzene (40.01 g,198.07 mmol), K₂CO₃ (54.75 g, 396.14 mmol), P_(d)(PPh₃)₄ (6.10 g, 5.28mmol) were added in a round bottom flask and THF (550 mL) and water (275mL) were added to dissolve and refluxed at 80° C. for 12 hours. When thereaction was completed, the temperature of the reaction was cooled toroom temperature, extracted with CH₂Cl₂ and wiped with water. Theorganic layer was dried over MgSO₄ and concentrated. The resultingcompound was separated by silicagel column chromatography to obtain theproduct. (46.00 g, 75%)

(3) Synthesis of Sub 1-1

Sub 1-II-1 (46.00 g, 99.03 mmol) and triphenylphosphine (64.93 g, 247.57mmol) were dissolved in o-dichlorobenzene (866 mL) and refluxed for 24hours. When the reaction was completed, the solvent was removed usingreduced pressure distillation. The resulting compound was separated bysilicagel column chromatography and recrystallized to obtain theproduct. (27.84 g, 65%)

Synthesis of Sub 1-24

(1) Synthesis of Sub 1-I-2

After 13-phenyl-13H-dibenzo[a,i]carbazole (52 g, 123.13 mmol),bis(pinacolato)diboron (34.39 g, 135.44 mmol), KOAc (36.25 g, 369.38mmol), PdCl₂(dppf) (3.02 g, 3.69 mmol) were dissolved in DMF (616 mL),and refluxed at 120° C. for 12 hours. When the reaction was completed,the temperature of the reaction was cooled to room temperature,extracted with CH₂Cl₂ and wiped with water. The organic layer was driedover MgSO₄ and concentrated. The resulting compound was recrystallizedby CH₂Cl₂ and methanol solvent to obtain the product. (49.13 g, 85%)

(2) Synthesis of Sub 1-II-2

Sub 1-I-2 (49.13 g, 104.67 mmol),5-(3-bromo-4-nitrophenyl)-5H-benzo[b]carbazole (65.51 g, 157.00 mmol),K₂CO₃ (43.40 g, 314.00 mmol), Pd(PPh₃)₄ (4.84 g, 4.19 mmol), THF (436mL) and water (218 ml) were carried out in the same manner as in Sub1-II-1 to give the product. (51.23 g, 72%).

(3) Synthesis of Sub 1-24

Sub 1-II-2 (51.23 g, 75.36 mmol), triphenylphosphine (49.42 g, 188.41mmol) and o-dichlorobenzene (659 mL) were carried out in the same manneras in Sub 1-1 to give the product Sub 1-24. (30.76 g, 63%).

Synthesis of Sub 1-26

(1) Synthesis of Sub 1-I-3

After 13-phenyl-13H-dibenzo[a,i]carbazole (45 g, 106.55 mmol),bis(pinacolato)diboron (29.76 g, 117.21 mmol), KOAc (31.37 g, 319.66mmol), PdCl₂(dppf) (261 g, 3.21 mmol) were dissolved in DMF (533 mL),and refluxed at 120° C. for 12 hours. When the reaction was completed,the temperature of the reaction was cooled to room temperature,extracted with CH₂Cl₂ and wiped with water. The organic layer was driedover MgSO₄ and concentrated. The resulting compound was recrystallizedby CH₂Cl₂ and methanol solvent to obtain the product. (37.51 g, 75%)

(2) Synthesis of Sub 1-II-3

Sub 1-I-3 (37.51 g, 79.91 mmol),4-(3-bromo-2-nitrophenyl)-13,13-dimethyl-13H-indeno[1,2-I]phenanthrene(59.26 g, 119.87 mmol), K₂CO₃ (33.13 g, 239.74 mmol), Pd(PPh₃)₄ (3.69 g,3.20 mmol), THF (333 mL) and water (166 ml) were carried out in the samemanner as in Sub 1-II-1 to give the product. (41.13 g, 68%).

(3) Synthesis of Sub 1-26

Sub 1-II-3 (41.13 g, 54.34 mmol), triphenylphosphine (35.63 g, 135.85mmol), o-dichlorobenzene (475 mL) were carried out in the same manner asin Sub 1-1 to give the product Sub 1-26. (23.24 g, 59%).

Synthesis of Sub 1-33

(1) Synthesis of Sub 1-I-4

After dinaphtho[1,2-b:2′,1-d]thiophene (60 g, 465.17 mmol),bis(pinacolato)diboron (46.14 g, 181.68 mmol), KOAc (48.63 g, 495.50mmol), PdCl₂(dppf) (4.05 g, 4.92 mmol) were dissolved in DMF (826 mL),and refluxed at 120° C. for 12 hours. When the reaction was completed,the temperature of the reaction was cooled to room temperature,extracted with CH₂Cl₂ and wiped with water. The organic layer was driedover MgSO₄ and concentrated. The resulting compound was recrystallizedby CH₂Cl₂ and methanol solvent to obtain the product. (56.25 g, 83%)

(2) Synthesis of Sub 1-II-4

Sub 1-I-1 (56.25 g, 137.08 mmol), 1-bromo-2-nitrobenzene (41.54 g,205.62 mmol), K₂CO₃ (56.84 g, 411.24 mmol), P_(d)(PPh₃)₄ (6.34 g, 5.48mmol), THF (571 mL) and water (286 ml) were carried out in the samemanner as in Sub 1-II-1 to give the product. (43.35 g, 78%).

(3) Synthesis of Sub 1-33

Sub 1-II-4 (43.35 g, 106.91 mmol), triphenylphosphine (70.11 g, 267.28mmol), o-dichlorobenzene (935 mL) were carried out in the same manner asin Sub 1-1 to give the product Sub 1-33. (27.95 g, 70%).

Synthesis of Sub 1-45

(1) Synthesis of Sub 1-I-5

After dinaphtho[1,2-b:2′,1-d]furan (60 g, 223.61 mmol),bis(pinacolato)diboron (62.46 g, 245.97 mmol), KOAc (65.84 g, 670.84mmol), PdCl₂(dppf) (5.48 g, 6.71 mmol) were dissolved in DMF (1118 mL),and refluxed at 120° C. for 12 hours. When the reaction was completed,the temperature of the reaction was cooled to room temperature,extracted with CH₂Cl₂ and wiped with water. The organic layer was driedover MgSO₄ and concentrated. The resulting compound was recrystallizedby CH₂Cl₂ and methanol solvent to obtain the product. (68.77 g, 78%)

(2) Synthesis of Sub 1-II-5

Sub 1-I-1 (68.77 g, 174.42 mmol), 1-bromo-2-nitrobenzene (52.85 g,261.63 mmol), K₂CO₃ (72.32 g, 523.26 mmol), P_(d)(PPh₃)₄ (8.06 g, 6.98mmol), THF (727 mL) and water (363 ml) were carried out in the samemanner as in Sub 1-II-1 to give the product. (49.58 g, 73%).

(3) Synthesis of Sub 1-45

Sub 1-II-5 (49.58 g, 127.32 mmol), triphenylphosphine (83.49 g, 318.30mmol), o-dichlorobenzene (1114 mL) were carried out in the same manneras in Sub 1-1 to give the product Sub 1-45. (30.94 g, 68%).

Synthesis of Sub 1-46

(1) Synthesis of Sub 1-I-6

After dinaphtho[1,2-b:2′,1-d]furan (55 g, 204.98 mmol),bis(pinacolato)diboron (57.26 g, 225.48 mmol), KOAc (60.35 g, 614.94mmol), PdCl₂(dppf) (5.02 g, 6.15 mmol) were dissolved in DMF (1025 mL),and refluxed at 120° C. for 12 hours. When the reaction was completed,the temperature of the reaction was cooled to room temperature,extracted with CH₂Cl₂ and wiped with water. The organic layer was driedover MgSO₄ and concentrated. The resulting compound was recrystallizedby CH₂Cl₂ and methanol solvent to obtain the product. (58.19 g, 72%)

(2) Synthesis of Sub 1-II-6

Sub 1-I-1 (58.19 g, 204.98 mmol),1-(3-bromo-4-nitrophenyl)-7-phenylphthalazine (89.93 g, 221.38 mmol),K₂CO₃ (61.19 g, 442.76 mmol), Pd(PPh₃)₄ (6.82 g, 5.90 mmol), THF (615mL) and water (307 ml) were carried out in the same manner as in Sub1-II-1 to give the product. (59.58 g, 68%).

(3) Synthesis of Sub 1-46

Sub 1-II-6 (59.58 g, 100.36 mmol), triphenylphosphine (65.81 g, 250.91mmol), o-dichlorobenzene (878 mL) were carried out in the same manner asin Sub 1-1 to give the product Sub 1-46. (36.64 g, 65%).

The compounds belonging to Sub 1 may be, but not limited to, thefollowing compounds, and Table 1 shows FD-MS (Field Desorption-MassSpectrometry) values of Sub 1 compounds.

Examples of Sub 1 include, but are not limited to, the followings.

TABLE 1 compound FD-MS compound FD-MS Sub 1-1 m/z = 432.16(C₃₂H₂₀N₂ =432.53) Sub 1-2 m/z = 508.19(C₃₈H₂₄N₂ = 508.62) Sub 1-3 m/z = 548.23(C₄₁H₂₈N₂ = 548.69) Sub 1-4 m/z = 538.15 (C₃₈H₂₂N₂S = 538.67) Sub 1-5m/z = 672.26 (C₅₁H₃₂N₂ = 672.83) Sub 1-7 m/z = 560.20 (C₄₀H₂₄N₄ =560.66) Sub 1-8 m/z = 664.20 (C₄₈H₂₈N₂S = 664.83) Sub 1-9 m/z = 610.22(C₄₄H₂₆N₄ = 610.72) Sub 1-10 m/z = 662.25 (C₄₈H₃₀N₄ = 662.80) Sub 1-11m/z = 582.21 (C₄₄H₂₆N₂ = 582.71) Sub 1-12 m/z = 587.21 (C₄₁H₂₅N₅ =587.69) Sub 1-13 m/z = 587.21 (C₄₁H₂₅N₅ = 587.69) Sub 1-14 m/z = 634.23(C₄₅H₂₈N₄ = 624.75) Sub 1-15 m/z = 549.21 (C₃₉H₂₅N₄ = 549.66) Sub 1-16m/z = 462.17 (C₃₃H₂₂N₂O = 462.55) Sub 1-17 m/z = 472.19 (C₃₅H₂₄N₂ =472.59) Sub 1-18 m/z = 600.20 (C₄₂H₂₄N₄O = 600.68) Sub 1-20 m/z = 751.27(C₅₄H₃₃N₅ = 751.89) Sub 1-21 m/z = 508.19 (C₃₈H₂₄N₂ = 508.62) Sub 1-22m/z = 746.27 (C₅₇H₃₄N₂ = 746.91) Sub 1-23 m/z = 673.25 (C₅₀H₃₁N₃ =673.82) Sub 1-24 m/z = 647.24 (C₄₈H₂₉N₃ = 647.78) Sub 1-25 m/z = 635.24(C₄₇H₂₉N₃ = 635.77) Sub 1-29 m/z = 649.25 (C₄₈H₃₁N₃ = 649.80) Sub 1-30m/z = 468.14 (C₃₂H₁₈F₂N₂ = 468.51) Sub 1-31 m/z = 736.26 (C₅₄H₃₂N₄ =736.88) Sub 1-32 m/z = 663.24 (C₄₇H₂₉N₅ = 663.78) Sub 1-33 m/z = 373.09(C₂₆H₁₅NS = 373.47) Sub 1-34 m/z = 601.19 (C₄₄H₂₇NS = 601.77) Sub 1-35m/z = 590.18 (C₄₂H₂₆N₂S = 590.74) Sub 1-36 m/z = 580.17 (C₃₉H₂₄N₄S =580.71) Sub 1-37 m/z = 737.22 (C₅₅H₃₁NS = 737.92) Sub 1-38 m/z = 530.19(C₃₈H₁₈D₅NS = 530.70) Sub 1-40 m/z = 692.23 (C₅₀H₃₂N₂S = 692.88) Sub1-42 m/z = 653.19 (C₄₆H₂₇N₃S = 653.80) Sub 1-43 m/z = 615.18 (C₄₃H₂₅N₃S= 615.75) Sub 1-44 m/z = 664.20 (C₄₈H₂₈N₂S = 664.83) Sub 1-45 m/z =357.12 (C₂₆H₁₅NO = 357.41) Sub 1-46 m/z = 561.18 (C₄₀H₂₃N₃O = 561.64)Sub 1-47 m/z = 637.23 (C₄₅H₂₇N₅ = 637.75) Sub 1-48 m/z = 558.21(C₄₂H₂₆N₂ = 558.68) Sub 1-51 m/z = 687.24 (C₄₉H₂₉N₅ = 687.81) Sub 1-52m/z = 423.11 (C₃₀H₁₇NS = 423.53) Sub 1-54 m/z = 457.15 (C₃₄H₁₉NO =457.53) Sub 1-55 m/z = 407.13 (C₃₀H₁₇NO = 407.47)2. Synthesis of Sub 2

Sub 2 of Reaction Scheme 3 can be synthesized by the reaction path ofthe following Reaction Scheme 3, but is not limited thereto.

(Hal¹=I, Br, Cl; Hal²=Br, Cl)

<Reaction Scheme 3>

Synthesis of Sub 2-18

(1) Synthesis of Sub 2-I-1

The starting material, 1-amino-2-naphthoic acid (CAS Registry Number:4919-43-1) (75.11 g, 401.25 mmol), was placed in a round bottom flaskwith urea (CAS Registry Number: 57-13-6) (168.69 g, 2808.75 mmol) andstirred at 160° C. After confirming the reaction by TLC, the reactionmixture was cooled to 100° C., water (200 ml) was added, and the mixturewas stirred for 1 hour. When the reaction was completed, the resultingsolid was filtered under reduced pressure, washed with water, and thendried to obtain 63.86 g (yield: 75%) of the product.

(2) Synthesis of Sub 2-II-1

Sub 2-I-1 (63.86 g, 300.94 mmol) was dissolved in POCl₃ (200 ml) at roomtemperature in a round bottom flask, and N, N-Diisopropylethylamine(97.23 g, 752.36 mmol) was slowly added dropwise thereto, followed bystirring at 90° C. After the reaction was completed, the reactionmixture was concentrated, and then ice water (500 ml) was added thereto,followed by stirring at room temperature for 1 hour. The resulting solidwas filtered under reduced pressure and dried to obtain 67.47 g (yield:90%) of the product.

(3) Synthesis of Sub 2-18

After Sub 2-II-1 (67.47 g, 270.86 mmol) was dissolved in THF (950 ml) ina round bottom flask, 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane(CAS Registry Number: 24388-23-6) (60.80 g, 297.94 mmol), Pd(PPh₃)₄(12.52 g, 10.83 mmol), K₂CO₃ (112.30 g, 812.57 mmol) and water (475 mL)were added to dissolve and stirred at 90° C. After the reaction wascompleted, the reaction mixture was extracted with CH₂Cl₂ and water. Theorganic layer was dried over MgSO₄ and concentrated. The resultingcompound was purified by silicagel column and recrystallized to obtain44.89 g (yield: 57%) of the product.

Synthesis of Sub 2-35

Sub 2-II-1 (19 g, 76.28 mmol),2-(dibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CASRegistry Number: 1822310-41-7) (26.92 g, 91.53 mmol), Pd(PPh₃)₄ (3.53 g,3.05 mmol), K₂CO₃ (31.63 g, 228.83 mmol), THF (280 ml) and water (140ml) were added and carried out in the same manner as in Sub 2-18 to givethe product. (15.69 g, 54%).

Synthesis of Sub 4-49

[1]Benzothieno[2,3-d]pyrimidine, 2,4-dichloro- (CAS Registry Number:76872-40-7) (32.01 g, 125.47 mmol), 1,3,2-Dioxaborolane,4,4,5,5-tetramethyl-2-(2-naphthalenyl) (CAS Registry Number:256652-04-7) (38.26 g, 150.56 mmol), Pd(PPh₃)₄ (5.80 g, 5.02 mmol),K₂CO₃ (52.02 g, 376.41 mmol), THF (460 ml) and water (230 ml) were addedand carried out in the same manner as in Sub 2-18 to give the product.(19.58 g, 45%).

The compounds belonging to Sub 2 may be, but not limited to, thefollowing compounds, and Table 2 shows FD-MS (Field Desorption-MassSpectrometry) values of Sub 2 compounds.

Examples of Sub 2 include, but are not limited to, the followings.

TABLE 2 compound FD-MS compound FD-MS Sub 2-1 m/z = 155.96 (C₆H₅Br =157.01) Sub 2-2 m/z = 205.97 (C₁₀H₇Br = 207.07) Sub 2-3 m/z = 245.97(C₁₂H₇BrO = 247.09) Sub 2-4 m/z = 113.00 (C₅H₄ClN = 113.54) Sub 2-5 m/z= 372.01 (C₂₂H₁₃BrO = 373.25) Sub 2-6 m/z = 296.02 (C₁₆H₉ClN₂S = 296.77)Sub 2-8 m/z = 266.06 (C₁₆H₁₁ClN₂ = 266.73) Sub 2-9 m/z = 310.01(C₁₆H₁₁BrN₂ = 311.18) Sub 2-11 m/z = 114.00 (C₄H₃ClN₂ = 114.53) Sub 2-12m/z = 113.00 (C₅H₄ClN = 113.54) Sub 2-13 m/z = 358.09 (C₂₂H₁₅ClN₂O =358.83) Sub 2-14 m/z = 290.06 (C₁₈H₁₁ClN₂ = 290.75) Sub 2-15 m/z =245.08 (C₁₄H₄D₅ClN₂ = 245.72) Sub 2-16 m/z = 392.11 (C₂₆H₁₇ClN₂ =392.89) Sub 2-17 m/z = 282.00 (C₆H₁₁Br = 283.17) Sub 2-18 m/z = 290.06(C₁₈H₁₁ClN₂ = 290.75) Sub 2-19 m/z = 255.99 (C₁₄H₉Br = 257.13) Sub 2-20m/z = 308.02 (C₁₈H₁₃Br = 309.21) Sub 2-21 m/z = 231.99 (C₁₂H₉Br =233.11) Sub 2-22 m/z = 279.08 (C₁₈H₁₄ClN = 279.77) Sub 2-23 m/z = 279.99(C₁₆H₉Br = 281.15) Sub 2-26 m/z = 386.04 (C₂₂H₁₅BrN₂ = 387.28) Sub 2-27m/z = 253.04 (C₁₄H₈ClN₃ = 253.69) Sub 2-28 m/z = 267.06 (C₁₅H₁₀ClN₃ =267.72) Sub 2-31 m/z = 492.03 (C₂₈H₁₇BrN₂S = 493.42) Sub 2-32 m/z =326.02 (C₁₅H₁₁BrN₄ = 327.17) Sub 2-33 m/z = 432.10 (C₂₈H₁₇ClN₂O =432.91) Sub 2-34 m/z = 396.05 (C₂₄H₁₃ClN₂S = 396.89) Sub 2-35 m/z =380.07 (C₂₄H₁₃ClN₂O = 380.83) Sub 2-36 m/z = 256.08 (C₁₅H₁₃ClN₂ =256.73) Sub 2-37 m/z = 311.02 (C₁₇H₁₀ClNOS = 311.78) Sub 2-38 m/z =162.00 (C₆H₁₁Br = 163.06) Sub 2-55 m/z = 317.07 (C₁₉H₁₂ClN₃ = 317.78)Synthesis Example of Final Products

Sub 1(1 eq.) was dissolved in toluene in a round bottom flask, and Sub2(1 eq.), Pd₂(dba)₃ (0.03 eq.), P(t-Bu)₃ (0.1 eq.), NaOt-Bu (3 eq.) wereadded and stirred at 100° C. When the reaction was complete, thereaction mixture was extracted with CH₂Cl₂ and water. The organic layerwas dried over MgSO₄ and concentrated. The resulting compound wasseparated by silicagel column chromatography and recrystallization toobtain the Final products.

Synthesis of 1-1

Sub 1-1(5.85 g, 13.53 mmol) was dissolved in toluene (135 ml) in a roundbottom flask, and Sub 2-1 (2.12 g, 13.53 mmol), Pd₂(dba)₃ (0.37 g, 0.41mmol), P(t-Bu)₃ (0.16 g, 0.81 mmol), NaOt-Bu (3.90 g, 40.58 mmol) wereadded and stirred at 100° C. When the reaction was complete, thereaction mixture was extracted with CH₂Cl₂ and water. The organic layerwas dried over MgSO₄ and concentrated. The resulting compound wasseparated by silicagel column chromatography and recrystallization toobtain 5.43 g of product. (yield: 79%)

Synthesis of 1-12

Sub 1-1 (5.85 g, 13.53 mmol), toluene (135 ml), Sub 4-42 (4.01 g, 13.53mmol), Pd₂(dba)₃ (0.37 g, 0.41 mmol), P(t-Bu)₃ (0.16 g, 0.81 mmol),NaOt-Bu (3.90 g, 40.58 mmol) were carried out in the same manner as 1-1to obtain 6.65 g of the product (yield: 71%)

Synthesis of 1-26

Sub 1-1 (5.85 g, 13.53 mmol), toluene (135 ml), Sub 2-15 (3.32 g, 13.53mmol), Pd₂(dba)₃ (0.37 g, 0.41 mmol), P(t-Bu)₃ (0.16 g, 0.81 mmol),NaOt-Bu (3.90 g, 40.58 mmol) were carried out in the same manner as 1-1to obtain 5.90 g of the product (yield: 68%)

Synthesis of 1-27

Sub 1-18 (7.85 g, 13.07 mmol), toluene (131 ml), Sub 2-1 (2.05 g, 13.07mmol), Pd₂(dba)₃ (0.36 g, 0.39 mmol), P(t-Bu)₃ (0.16 g, 0.78 mmol),NaOt-Bu (3.77 g, 39.21 mmol) were carried out in the same manner as 1-1to obtain 6.46 g of the product (yield: 73%)

Synthesis of 1-33

Sub 1-24 (10.00 g, 15.44 mmol), toluene (154 ml), Sub 2-1 (2.42 g, 15.44mmol), Pd₂(dba)₃ (0.42 g, 0.46 mmol), P(t-Bu)₃ (0.19 g, 0.93 mmol),NaOt-Bu (4.45 g, 46.31 mmol) were carried out in the same manner as 1-1to obtain 7.84 g of the product (yield: 75%)

Synthesis of 1-47

Sub 1-33 (6.55 g, 17.54 mmol), toluene (175 ml), Sub 2-21 (4.91 g, 17.54mmol), Pd₂(dba)₃ (0.48 g, 0.53 mmol), P(t-Bu)₃ (0.21 g, 1.05 mmol),NaOt-Bu (5.06 g, 52.61 mmol) were carried out in the same manner as 1-1to obtain 8.44 g of the product (yield: 78%)

Synthesis of 1-54

Sub 1-33 (6.55 g, 17.54 mmol), toluene (175 ml), Sub 2-21 (4.70 g, 17.54mmol), Pd₂(dba)₃ (0.48 g, 0.53 mmol), P(t-Bu)₃ (0.21 g, 1.05 mmol),NaOt-Bu (5.06 g, 52.61 mmol) were carried out in the same manner as 1-1to obtain 8.38 g of the product (yield: 79%)

Synthesis of 1-74

Sub 1-33 (8.57 g, 22.95 mmol), toluene (229 ml), Sub 2-42 (12.13 g,22.95 mmol), Pd₂(dba)₃ (0.63 g, 0.69 mmol), P(t-Bu)₃ (0.28 g, 1.38mmol), NaOt-Bu (6.62 g, 68.84 mmol) were carried out in the same manneras 1-1 to obtain 12.81 g of the product (yield: 68%)

Synthesis of 1-81

Sub 1-45 (7.21 g, 20.17 mmol), toluene (202 ml), Sub 2-47 (7.29 g, 20.17mmol), Pd₂(dba)₃ (0.55) were carried out in the same manner as 1-1 toobtain 10.16 g of the product (yield: 79%)

Synthesis of 1-90

Sub 1-45 (10.13 g, 28.34 mmol), toluene (283 ml), Sub 2-54 (8.24 g,28.34 mmol), Pd₂(dba)₃ (0.78 g, 0.85 mmol), P(t-Bu)₃ (0.34 g, 1.70mmol), NaOt-Bu (8.17 g, 85.03 mmol) were carried out in the same manneras 1-1 to obtain 13.35 g of the product (yield: 77%)

TABLE 3 compound FD-MS compound FD-MS 1-1 m/z = 508.19(C₃₈H₂₄N₂ =508.62) 1-2 m/z = 634.24(C₄₈H₃₀N₂ = 634.78) 1-3 m/z = 624.26(C₄₇H₃₂N₂ =624.79) 1-4 m/z = 614.18(C₄₄H₂₆N₂S = 614.77) 1-5 m/z = 598.20(C₄₄H₂₆N₂O= 598.71) 1-6 m/z = 748.29(C₅₇H₃₆N₂ = 748.93) 1-7 m/z = 824.32(C₆₃H₄₀N₂= 825.03) 1-8 m/z = 636.23(C₄₆H₂₈N₄ = 636.76) 1-9 m/z = 509.19(C₃₇H₂₃N₃= 509.61) 1-10 m/z = 740.23(C₅₄H₃₂N₂S = 740.92) 1-11 m/z =724.25(C₅₄H₃₂N₂O = 724.86) 1-12 m/z = 692.20(C₄₈H₂₈N₄S = 692.84) 1-13m/z = 736.26(C₅₄H₃₂N₄ = 736.88) 1-14 m/z = 662.25(C₄₈H₃₀N₄ = 662.80)1-15 m/z = 713.26(C₅₁H₃₁N₅ = 713.84) 1-16 m/z = 814.31(C₆₀H₃₈N₄ =814.99) 1-17 m/z = 658.24(C₅₀H₃₀N₂ = 658.80) 1-18 m/z = 663.24(C₄₇H₂₉N₅= 663.78) 1-19 m/z = 662.25(C₄₈H₃₀N₄ = 662.80) 1-20 m/z =662.25(C₄₈H₃₀N₄ = 662.80) 1-21 m/z = 663.24(C₄₇H₂₉N₅ = 663.78) 1-22 m/z= 702.25(C₄₉H₃₀N₆ = 702.82) 1-23 m/z = 626.23(C₄₄H₂₈N₅ = 626.74) 1-24m/z = 784.28(C₅₅H₃₆N₄O₂ = 784.92) 1-25 m/z = 726.28(C₅₃H₃₄N₄ = 726.88)1-26 m/z = 641.26(C₄₆H₂₃D₅N₄ = 641.79) 1-27 m/z = 677.22(C₄₇H₂₇N₅O =677.77) 1-28 m/z = 844.36(C₆₂H₄₄N₄ = 845.06) 1-29 m/z = 953.35(C₇₀H₄₃N₅= 954.15) 1-30 m/z = 584.23(C₄₄H₂₈N₂ = 584.72) 1-31 m/z =822.30(C₆₃H₃₈N₂ = 823.01) 1-32 m/z = 749.28(C₅₆H₃₅N₃ = 749.92) 1-33 m/z= 723.27(C₅₄H₃₃N₃ = 723.88) 1-34 m/z = 711.27(C₅₃H₃₃N₃ = 711.87) 1-35m/z = 800.32(C₆₁H₄₀N₂ = 801.01) 1-36 m/z = 827.33(C₆₂H₄₁N₃ = 828.03)1-37 m/z = 710.27(C₅₄H₃₄N₂ = 710.88) 1-38 m/z = 725.28(C₅₄H₃₅N₃ =725.90) 1-39 m/z = 544.18(C₃₈H₂₂F₂N₂ = 544.60) 1-40 m/z =812.29(C₆₀H₃₆N₄ = 812.98) 1-41 m/z = 917.33(C₆₅H₃₉N₇ = 918.08) 1-42 m/z= 449.12(C₃₂H₁₉NS = 449.57) 1-43 m/z = 499.14(C₃₆H₂₁NS = 499.63) 1-44m/z = 549.16(C₄₀H₂₃NS = 549.69) 1-45 m/z = 601.19(C₄₄H₂₇NS = 601.77)1-46 m/z = 525.16(C₃₈H₂₃NS = 525.67) 1-47 m/z = 616.20(C₄₄H₂₈N₂S =616.78) 1-48 m/z = 573.16(C₄₂H₂₃NS = 573.71) 1-49 m/z = 765.21(C₅₆H₃₁NOS= 765.93) 1-50 m/z = 551.17(C₄₀H₂₅NS = 551.71) 1-51 m/z =451.11(C₃₀H₁₇N₃S = 451.55) 1-52 m/z = 679.21(C₄₈H₂₉N₃S = 679.84) 1-53m/z = 590.16(C₄₀H₂₂N₄S = 590.70) 1-54 m/z = 604.17(C₄₁H₂₄N₄S = 604.73)1-55 m/z = 654.19(C₄₅H₂₆N₄S = 654.79) 1-56 m/z = 577.16(C40H23N3S =577.71) 1-57 m/z = 603.18(C₄₂H₂₅N₃S = 603.74) 1-58 m/z =785.20(C₅₄H₃₁N₃S₂ = 785.98) 1-59 m/z = 619.18(C₄₁H₂₅N₅S = 619.75) 1-60m/z = 769.22(C₅₄H₃₁N₃OS = 769.92) 1-61 m/z = 733.16(C₅₀H₂₇N₃S₂ = 733.91)1-62 m/z = 717.19(C₅₀H₂₇N₃OS = 717.85) 1-63 m/z = 593.19(C₄₁H₂₇N₃S =593.75) 1-64 m/z = 648.13(C₄₃H₂₄N₂OS₂ = 648.80) 1-65 m/z =601.19(C₄₄H₂₇NS = 601.77) 1-66 m/z = 455.17(C₃₂H₂₅NS = 455.62) 1-67 m/z= 894.28(C₆₄H₃₈N₄S = 895.10) 1-68 m/z = 659.19(C₄₂H₂₅N₇S = 659.77) 1-69m/z = 813.25(C₆₁H₃₅NS = 814.02) 1-70 m/z = 609.20(C₄₁H₁₉D₅N₄S = 609.76)1-71 m/z = 780.26(C₅₇H₃₆N₂S = 780.99) 1-72 m/z = 1035.36(C₇₆H₄₉N₃S =1036.31) 1-73 m/z = 876.24(C₆₀H₃₆N₄S₂ = 877.10) 1-74 m/z =820.20(C₅₈H₃₂N₂S₂ = 821.03) 1-75 m/z = 729.22(C₅₂H₃₁N₃S = 729.90) 1-76m/z = 769.23(C₅₃H₃₁N₅S = 769.93) 1-77 m/z = 741.22(C₅₃H₃₁N₃S = 741.91)1-78 m/z = 926.23(C₆₂H₃₄N₆S₂ = 927.12) 1-79 m/z = 433.15(C₃₂H₁₉NO =433.51) 1-80 m/z = 549.21(C₄₁H₂₇NO = 549.67) 1-81 m/z = 637.22(C₄₆H₂₇N₃O= 637.74) 1-82 m/z = 588.20(C₄₁H₂₄N₄O = 588.67) 1-83 m/z =638.21(C₄₅H₂₆N₄O = 638.73) 1-84 m/z = 561.18(C₄₀H₂₃N₃O = 561.64) 1-85m/z = 667.17(C₄₆H₂₅N₃OS = 667.79) 1-86 m/z = 617.16(C₄₂H₂₃N₃OS = 617.73)1-87 m/z = 601.18(C₄₂H₂₃N₃O₂ = 601.67) 1-88 m/z = 561.18(C₄₀H₂₃N₃O =561.64) 1-89 m/z = 588.20(C₄₁H₂₄N₄O = 588.67) 1-90 m/z =611.20(C₄₄H₂₅N₃O = 611.70) 1-91 m/z = 637.22(C₄₆H₂₇N₃O = 637.74) 1-92m/z = 684.26(C₅₂H₃₂N₂ = 684.84) 1-93 m/z = 713.26(C₅₁H₃₁N₅ = 713.84)1-94 m/z = 684.26(C₅₂H₃₂N₂ = 684.84) 1-95 m/z = 763.27(C₅₅H₃₃N₅ =763.90) 1-96 m/z = 651.20(C₄₈H₂₉NS = 651.83) 1-97 m/z = 704.20(C₄₉H₂₈N₄S= 704.85) 1-98 m/z = 654.19(C₄₅H₂₆N₄S = 654.79) 1-99 m/z =633.21(C₄₈H₂₇NO = 633.75) 1-100 m/z = 638.21(C₄₅H₂₆N₄O = 638.73) 1-101m/z = 688.23(C₄₉H₂₈N₄O = 688.79)

Otherwise, the synthesis examples of the present invention representedby Formula 1 have been described, but these are all based on theBuchwald-Hartwig cross coupling reaction, Suzuki cross-couplingreaction, Intramolecular acid-induced cyclization reaction (J. mater.Chem. 1999, 9, 2095.), Pd(II)-catalyzed oxidative cyclization reaction(Org. Lett. 2011, 13, 5504), Grignard reaction, Cyclic Dehydrationreaction and PPh₃-mediated reductive cyclization reaction (J. Org. Chem.2005, 70, 5014.), and those skilled in the art will readily understandthat the above reaction proceeds even when, besides the substituentspecified in the specific synthesis example, other substituents(substituents such as Ar¹ to Ar⁶, L¹ to L⁶, R¹ to R⁵, X¹, X², A and B)defined in Formula 1 are bonded.

Evaluation of Manufacture of Organic Electric Element

Example 1) Manufacture and Evaluation of Red Organic Light EmittingDiode (Phosphorescent Host)

On an ITO layer(anode) formed on a glass substrate, 2-TNATA wasvacuum-deposited to form a hole injection layer with a thickness of 60nm, and NPB was vacuum-deposited on the hole injection layer to form ahole transport layer with a thickness of 60 nm.

Then, the emitting layer was deposited on the hole transport layer at athickness of 30 nm by doping the inventive compound P 1-1 with the hostmaterial and [bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate](hereinafter abbreviated as(piq)₂Ir(acac)) with the dopant material at aweight ratio of 95:5. Next, BAlq was vacuum-deposited on the emittinglayer to a thickness of 10 nm to form a hole blocking layer, and Alq3was formed to a thickness of 40 nm on the hole blocking layer to form anelectron transport layer. Thereafter, LiF was deposited to a thicknessof 0.2 nm on the electron transport layer to form an electron injectionlayer, and then Al was deposited to a thickness of 150 nm on theelectron injection layer to form a cathode.

[Example 2] to [Example 37] Red Organic Light Emitting Diode

An organic electroluminescent device was prepared in the same manner asin Example 1, except that the compound of the present inventiondescribed in Table 4 was used instead of the compound 1-1 as the hostmaterial of the emitting layer.

Comparative Examples 1 to 4

An organic electroluminescent device was prepared in the same manner asin Example 1, except that comparative compound 1 to 4 described in Table4 was used instead of the compound 1-1 as the host material of theemitting layer.

To the OLEDs which were manufactured by example 1 to 30 and comparativeexamples 1 to 5, a forward bias direct current voltage was applied, andelectroluminescent(EL) properties were measured using PR-650 ofPhotoresearch Co., and T95 life was measured using a life measuringapparatus manufactured by McScience Inc. with a reference luminance of2500 cd/m². The measurement results are shown in Tables 4 below.

TABLE 4 Current Brightness Efficiency CIE compound Voltage Density(cd/m²) (cd/A) T(95) X Y comparative comparative 6.2 21.2 2500 11.8108.5 0.66 0.32 example(1) compound 1 comparative comparative 6.1 19.82500 12.6 110.8 0.66 0.32 example (2) compound 2 comparative comparative5.7 17.2 2500 14.5 113.5 0.66 0.32 example (3) compound 3 comparativecomparative 5.7 16.3 2500 15.3 114.3 0.66 0.32 example (4) compound 4example(1) compound 1-1 5.3 11.4 2500 21.9 134.7 0.66 0.32 example(2)compound 1- 5.3 11.7 2500 21.3 134.3 0.66 0.32  2 example(3) compound 1-5.3 11.5 2500 21.7 132.8 0.66 0.33  3 example(4) compound 1- 5.1 10.22500 24.4 147.0 0.66 0.32  4 example(5) compound 1- 5.0 9.9 2500 25.3149.1 0.66 0.33  8 example(6) compound 1- 5.0 10.0 2500 25.1 148.6 0.660.33 12 example(7) compound 1- 5.1 10.2 2500 24.6 147.1 0.66 0.32 13example(8) compound 1- 5.0 10.0 2500 24.9 147.8 0.66 0.33 15 example(9)compound 1- 5.3 11.2 2500 22.3 135.6 0.66 0.33 16 example(10) compound1- 5.3 11.6 2500 21.5 132.2 0.66 0.33 17 example(11) compound 1- 5.010.1 2500 24.8 147.5 0.66 0.33 18 example(12) compound 1- 5.4 13.7 250018.3 127.1 0.66 0.32 30 example(13) compound 1- 5.4 13.4 2500 18.7 128.40.66 0.32 33 example(14) compound 1- 5.4 12.8 2500 19.5 128.3 0.66 0.3341 example(15) compound 1- 5.2 10.5 2500 23.7 143.4 0.66 0.33 42example(16) compound 1- 5.2 10.6 2500 23.5 142.9 0.66 0.33 43example(17) compound 1- 5.2 10.8 2500 23.2 142.6 0.66 0.33 45example(18) compound 1- 5.2 10.5 2500 23.9 144.3 0.66 0.32 52example(19) compound 1- 4.9 9.2 2500 27.3 156.7 0.66 0.32 54 example(20)compound 1- 4.9 9.1 2500 27.5 154.3 0.66 0.32 55 example(21) compound 1-4.9 9.0 2500 27.9 156.9 0.66 0.32 56 example(22) compound 1- 5.2 10.32500 24.2 145.9 0.66 0.33 58 example(23) compound 1- 4.9 9.3 2500 27.0155.7 0.66 0.33 60 example(24) compound 1- 4.9 9.3 2500 26.8 154.1 0.660.32 61 example(25) compound 1- 5.4 12.4 2500 20.1 129.7 0.66 0.33 65example(26) compound 1- 5.4 12.1 2500 20.7 131.8 0.66 0.33 75example(27) compound 1- 5.3 11.0 2500 22.8 136.4 0.66 0.33 79example(28) compound 1- 5.3 10.9 2500 22.9 137.0 0.66 0.33 81example(29) compound 1- 5.0 9.5 2500 26.2 153.4 0.66 0.32 82 example(30)compound 1- 5.0 9.7 2500 25.9 152.7 0.66 0.33 83 example(31) compound 1-5.0 9.4 2500 26.7 153.6 0.66 0.33 84 example(32) compound 1- 5.1 9.62500 26.0 152.5 0.66 0.33 85 example(33) compound 1- 5.1 9.7 2500 25.7149.8 0.66 0.33 87 example(34) compound 1- 5.1 9.8 2500 25.4 149.3 0.660.33 90 example(35) compound 1- 5.3 11.8 2500 21.1 131.3 0.66 0.32 93example(36) compound 1- 5.2 10.9 2500 23.0 137.3 0.66 0.33 98example(37) compound 1- 5.3 11.1 2500 22.6 135.9 0.66 0.33 100 

As can be seen from the results of Table 4, it can be confirmed that thedevice using the compound according to one embodiment of the presentinvention as the phosphorescent host material of the emitting layer issignificantly improved in electrical characteristics as compared withthe device using Comparative Compounds 1 to 4 as the phosphorescent hostmaterial in the emitting layer.

First, comparing Comparative Example 1 with Comparative Example 2,Comparative Example 2 using the comparative compound 2, which is aheterophasic ring compound having different hetero atoms (N, S), shows ahigher efficiency than Comparative Example 1 using Comparative Compound1 having the same nitrogen atom. Also, by comparing the compounds 1-8,1-56 and 1-84 of the present invention, it can be seen that the deviceof the compound having heteroatom of the dissimilar type exhibits theimproved electrical characteristic more than the device of the compoundhaving the heteroatom of the same type.

Compounds having different heteroatoms has an antiparallelcofacialπ-stacking structure in which the packing structure of the moleculefaces in the opposite direction rather than the compounds having thesame heteroatom.

Thus, the arrangement order of the molecules is made face-to-face, andit is considered that the steric effect of Ar¹ of the asymmetricallyarranged hetero atom N, which is the cause of the stacking structure,results in remarkably high carrier mobility and thus has a highefficiency, and the lifetime is remarkably increased due to highoxidation stability.

In addition, Comparative Compounds 3 and 4, which are 6-ring compoundsin which benzene is fused at a specific position of Comparative Compound2, showed excellent results in terms of driving voltage, efficiency, andlifetime. Further, it can be seen that the compound of the presentinvention, which is a 7-ring compound in which benzene is fused at aspecific position more than the Comparative compound 3, shows remarkablyexcellent results in terms of all the electrical characteristics of thedevice. This indicates that the device has an excellent device resultbecause one more benzene is fused at a specific position, the T1 valueof the compound is lowered, the charge transfer from the host to thedopant is smooth, and the charge balance in the emitting layer isincreased.

As a result, through comparison of the comparative compounds 1 to 4 andthe inventive example compounds, since the energy level of the compoundvaries depending on the number of the compound rings, the compounds ofthe present invention have appropriate HOMO and LUMO energies comparedwith Comparative Compounds 1 to 4, and the charge balance in theemitting layer of holes and electrons is increased, therefore the deviceresult is improved as compared with the comparative example device usingthe comparative compound.

On the other hand, in the device result of the embodiment of the presentinvention, it can be confirmed that the chemical properties such as theenergy band gap and the device characteristics such as the packingdensity are remarkably changed due to the introduction of a specificsubstituent group to the hetero atom N in the same core. That is, it canbe seen that the driving voltage, efficiency and lifetime of the deviceare improved by introducing a specific substituent such as a heteroarylgroup other than a simple aryl group into N.

Although exemplary embodiments of the present invention have beendescribed for illustrative purposes, those skilled in the art willappreciate that various modifications, additions and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims. Therefore, the embodimentdisclosed in the present invention is intended to illustrate the scopeof the technical idea of the present invention, and the scope of thepresent invention is not limited by the embodiment.

The scope of the present invention shall be construed on the basis ofthe accompanying claims, and it shall be construed that all of thetechnical ideas included within the scope equivalent to the claimsbelong to the present invention.

What is claimed is:
 1. A compound represented by Formula 1:

wherein: 1) X is N-L²-Ar², O or S, 2) Ar¹ and Ar² are each independently selected from the group consisting of hydrogen; deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R^(a))(R^(b)); 3) a and b are an integer of 0 to 4, and c is an integer of 0 to 6, 4) R¹, R² and R³ are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R^(a))(R^(b)); or in case a, b and c are 2 or more, and R¹, R² and R³ are each in plural being the same or different, a plurality of R¹ or a plurality of R² or a plurality of R³ may be bonded to each other to form a ring, with the proviso that the plurality of R¹ does not form a heterocyclic ring, with the proviso that R¹ is not halogen, and with the proviso that where X is O or S, R³ is hydrogen, 5) L¹ and L² are each independently selected from the group consisting of a single bond; a C₆-C₆₀ arylene group; and a fluorenylene group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group; 6) L′ is selected from the group consisting of a single bond; a C₆-C₆₀ arylene group; and a fluorenylene group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group; and R^(a) and R^(b) are each independently selected from the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si, or P, wherein, the aryl group, fluorenyl group, arylene group, heterocyclic group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; a silane group substituted or unsubstituted with C₁-C₂₀ alkyl group or C₆-C₂₀ aryl group; siloxane group; boron group; germanium group; cyano group; nitro group; -L′-N(R^(a))(R^(b)); a C₁-C₂₀ alkylthio group; C₁-C₂₀ alkoxyl group; C₁-C₂₀ alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynyl group; C₆-C₂₀ aryl group; C₆-C₂₀ aryl group substituted with deuterium; a fluorenyl group; C₂-C₂₀ heterocyclic group; C₃-C₂₀ cycloalkyl group; C₇-C₂₀ arylalkyl group; and C₈-C₂₀ arylalkenyl group; wherein the substituents may combine each other and form a saturated or unsaturated ring, wherein the term ‘ring’ means a C₃-C₆₀ aliphatic ring or a C₆-C₆₀ aromatic ring or a C₂-C₆₀ heterocyclic group or a fused ring formed by the combination of thereof.
 2. The compound of claim 1, wherein the compound represented by Formula 1 is represented by any one of the following Formulas 2 to 4:

wherein R¹, R², R³, L¹, L², Ar¹, Ar², a, b and c are the same as defined in claim
 1. 3. The compound of claim 1, wherein Ar¹ or Ar² in Formula 1 are represented by Formula A-1 or A-2:

wherein: 1) Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, Q⁷, Q⁸ and Q⁹ are each independently N or CR^(e), 2) R^(e) is selected from the group consisting of hydrogen; deuterium; halogen; a silane group substituted or unsubstituted with C₁-C₂₀ alkyl group or C₆-C₂₀ aryl group; siloxane group; boron group; germanium group; cyano group; nitro group; a C₁-C₂₀ alkylthio group; C₁-C₂₀ alkoxyl group; C₁-C₂₀ alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynyl group; C₆-C₂₀ aryl group; C₆-C₂₀ aryl group substituted with deuterium; a fluorenyl group; C₂-C₂₀ heterocyclic group; containing at least one hetero atom of O, N, S, Si, or P, C₃-C₂₀ cycloalkyl group; C₇-C₂₀ arylalkyl group; and C₈-C₂₀ arylalkenyl group; 3) Z is any one of Formulas C-1 to C-15:

wherein the mark * represents a bonding moiety which combines with the ring including Q1 to Q4 to form a fused ring, 4) in Formulas C-11 to C-15, W¹ and W² are single bond, N-L³-Ar³, S, O or C(R^(f))(R^(g)), 5) V is each independently N or CR^(h), 6) L³ is selected from a single bond; a C₆-C₆₀ arylene group; and a fluorenylene group; C₂-C₆₀ divalent heterocyclic group containing at least one hetero atom of O, N, S, Si, or P; a divalent fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a divalent aliphatic hydrocarbon group; 7) Ar³, R^(f), R^(g) and R^(h) are each independently selected from the aryl group, fluorenyl group, a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; R^(f) and R^(g) may be bonded to each other to form a spiro together with the carbon (C) to which they are bonded.
 4. A compound selected from the group consisting of the following compounds 1-1 to 1-101:


5. An organic electronic element comprising: a first electrode; a second electrode; and an organic material layer disposed between the first electrode and the second electrode, wherein the organic material layer comprises a compound according to claim
 1. 6. The organic electronic element according to claim 5, wherein the organic material layer is selected from the group consisting of a hole injection layer, a hole transport layer, an emitting auxiliary layer and emitting layer.
 7. The organic electronic element according to claim 6, wherein the compound is used as a phosphorescent host material of the emitting layer.
 8. The organic electronic element according to claim 5, wherein the organic material layer is formed by one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process.
 9. A display device comprising the organic electronic element of claim 5, and a control part driving the display device.
 10. The display device according to claim 9, wherein the organic electronic element is at least one of an OLED, an organic solar cell, an organic photo conductor(OPC), organic transistor(organic TFT) and an element for monochromic or white illumination.
 11. An organic electronic element comprising: a first electrode; a second electrode; and an organic material layer disposed between the first electrode and the second electrode, wherein the organic material layer comprises a compound according to claim
 4. 12. A display device comprising the organic electronic element of claim 11; and a control part driving the display device. 